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Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

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The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the...
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Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

4.0K
Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
4.0K
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

2.8K
Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
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Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism01:26

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism

3.5K
The Hofmann and Curtius rearrangement reactions can be applied to synthesize primary amines from carboxylic acid derivatives such as amides and acyl azides. In the Hofmann rearrangement, a primary amide undergoes deprotonation in the presence of a base, followed by halogenation to generate an N-haloamide. A second proton abstraction produces a stabilized anionic species, which rearranges to an isocyanate intermediate via an alkyl group migration from the carbonyl carbon to the neighboring...
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Amines to Sulfonamides: The Hinsberg Test01:23

Amines to Sulfonamides: The Hinsberg Test

3.6K
The Hinsberg test is a method to identify primary, secondary and tertiary amines, named after its pioneer, Oscar Hinsberg. Here, amines are treated with benzenesulfonyl chloride, also known as the Hinsberg reagent, in the presence of an excess of aqueous base, followed by acidification. Based on the nature of the amines, different changes are observed.
Generally, a primary amine reacts with the Hinsberg reagent to produce an N-substituted benzenesulfonamide. The electron-withdrawing...
3.6K

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Investigation into a Conformationally Locked (Z)-Azidoxime.

Alexander H Cleveland1, Jack V Davis1, Gregory H Imler2

  • 1High Explosive Science and Technology, Los Alamos National Laboratory, Los Alamos, New Mexico 87545, United States.

The Journal of Organic Chemistry
|October 11, 2023
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1,2,4-triazine-derived azidoximes are poor candidates for energetic materials due to their inability to cyclize. Computational studies reveal a high activation energy barrier preventing isomerization to the reactive (E)-conformation.

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Area of Science:

  • Energetic materials
  • Organic chemistry
  • Computational chemistry

Background:

  • High-nitrogen compounds are crucial in propellants, explosives, and pharmaceuticals.
  • Azidoximes and 1-hydroxytetrazoles are classes of high-nitrogen materials.
  • Azidoximes are energetic but sensitive, often cyclized to stable isomers.

Purpose of the Study:

  • Investigate the unexpected lack of reactivity of novel 1,2,4-triazine-derived azidoximes.
  • Determine the underlying reasons for the failure of these compounds to cyclize.
  • Explore the potential of these azidoximes as energetic materials.

Main Methods:

  • Synthesis of novel 1,2,4-triazine-derived azidoximes.
  • Attempted cyclization under established conditions.
  • Density Functional Theory (DFT) investigations.
  • Electrostatic potential mapping based on crystallographic data.

Main Results:

  • 1,2,4-triazine-derived azidoximes did not cyclize under standard conditions, even with heating.
  • DFT calculations showed a high activation energy (26.4 kcal mol⁻¹) for isomerization.
  • The compounds are locked in a non-reactive (Z)-conformation, preventing cyclization.

Conclusions:

  • 1,2,4-triazine-based azidoximes are unsuitable for applications requiring cyclization to 1-hydroxytetrazoles.
  • The high activation energy barrier for isomerization is the primary reason for their lack of reactivity.
  • These findings highlight the importance of conformational analysis in designing new energetic materials.